#184 - My WORST client ever & why it matters
Have you ever agreed to work with a client despite your gut screaming “No”?
I have, and it didn’t end well.
Today I’m sharing a story that my clients have asked for again and again – my worst client experience ever. I’m not just complaining or airing grievances, I’m talking about the impact this experience had on how I approach my business and, more importantly, how I choose my clients.
For those who don't know me, my earlier career involved 12 years of litigation and dispute resolution. You’d think my worst client would stem from those stressful, high-stakes days in court, but no. My worst client came about four years ago in my current business—a mature female business owner with a well-established team.
The issues began when I agreed to a retainer arrangement, something I usually avoid because it doesn’t align with my business ethos. Despite my better judgement and intuition screaming a loud “No!”, I begrudgingly agreed, hoping it would work out. Spoiler alert: It did not.
Respect in business relationships is paramount. Unfortunately, this client lacked it entirely—not just for me, but for the value I bring. I was constantly micromanaged, with endless phone calls questioning my every move on time and tasks left on the retainer. It was toxic and exhausting.
So, what did I learn from this?
Firstly, respect is now a non-negotiable for me. If a client doesn't respect me, my time, or my work, it’s doomed from the start. I've learned to observe closely how potential clients treat their own teams and clients. Their behaviour is often a precursor to how they might treat me.
Additionally, I’ve learned to back myself, always. Self-doubt can be debilitating. When I doubt myself, the decisions that follow rarely serve me well. Each time I've ignored my intuition and agreed to terms that didn't sit right with me; I've lived to regret it.
So, that’s the story of my worst client ever.
While it's not the dramatic tale many might expect, I hope it encourages you to reflect on your own client experiences and make thoughtful changes. Evaluate those relationships, tweak your systems, and ensure that you’re working with people who respect and align with your values.
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[00:00:00] Tracey: Hello, everyone. Welcome back to another episode of the rise up in business podcast. I'm going to share with you today the story about my very worst client. I'm going to share this because I'm asked this a lot actually. Clients will often ask, particularly clients that I've developed a closer relationship with.
[00:00:41] Tracey: Gosh Tracy, talk to me about that. Your worst client, what's the worst client you've ever had? And this comes about in the context of developing documents for clients, the way that I do, because my approach is very holistic. So it's not just a, here's your documents. Good luck. See you later. I get involved in it's collaborative throughout.
[00:01:01] Tracey: That collaboration is opportunities for us to talk together. I ask questions. I hear stories, you know, we develop that rapport. And so I want to know the pain points and I want to know concerns and fears and things like that, because that's how I can develop documents that really work. So it's in that vein that I have these conversations with clients and colleagues and friends as well.
[00:01:28] Tracey: But I'm asked with real anticipation, gosh, Tracy, what's the worst client you've ever had? And for those who are new to the podcast or who don't know me, the earlier part of my career for 12 years was spent in litigation and dispute resolution. So I spent all my time in court acting for clients suing or being sued.
[00:01:49] Tracey: So it's really intense and stressful and you see all sorts of things. Gosh, we all know financial pressures and stress and worry really can bring out. The worst in people. I also did several years of criminal defense work and those who know me well know that I have lots of stories to share from that part of my career.
[00:02:09] Tracey: So when I'm asked the question around what was my worst client, I know people are waiting with bated breath thinking I'm going to tell them something salacious from back in those days. But that's not it. That's not it. Hands down. The worst client I've ever had was in this business about four years ago, female business owner, more mature lady with a team, very well established business owner.
[00:02:36] Tracey: She was my absolute worst client. It wasn't back in the litigation days. It wasn't criminal defense work. It absolutely wasn't. And the reason I'm sharing this is because let's think about what makes a client not aligned. This is not low vibing podcast. This is not negative, Nancy. This is very much a let's reframe it.
[00:03:03] Tracey: What can we learn to move forward in a really positive way? So it really matters to understand who was our worst client or what are our unaligned clients or who don't I want to act for? That's why I'm sharing this because I think this is such valuable food for thought. And this is an exercise that I think everybody can get something out of.
[00:03:24] Tracey: So back to what made this particular client, the worst client I've ever had was around two things, one respect and a complete sheer Yeah. Yeah. Lack of respect for what I do, for who I am, for the value I bring, I was very much treated like an admin support person. And I think that was because I was asked to enter into a retainer arrangement.
[00:03:54] Tracey: I don't do retainer work in this business. It doesn't suit my model. It's not aligned with my ethos. It's not consistent with my why I don't do it. I have done it a couple of times at the request of the client and against my better judgment. I've agreed begrudgingly because I knew intuitively it wasn't right.
[00:04:13] Tracey: And no happy endings to those relationships or those stories. It just doesn't end well. It didn't end well. And this particular one didn't end well either, but this is where It went wrong. It started wrong from the outset. I was persuaded to do something that I didn't want to do, but I did it anyway. And oh gosh, don't we all have a story like that?
[00:04:35] Tracey: probably more than one actually, where we've done something that we didn't want to do. We doubted ourselves. We didn't back ourselves. We did it for the right reasons, hand on heart, because we thought that it would be okay because the client really wanted it or somebody else asked and it didn't pan out the way that we'd hoped and in fact we should have stood firm on our ground.
[00:04:58] Tracey: Stuck to the decision we wanted to make, which was a hard no rather than questioning ourselves. Yes, I know we've all got stories like that. And that's the beginning and end of this story because I'd agreed to do retainer work. And as a result, it was very difficult to manage expectations such that I then fell into being treated like an admin person.
[00:05:18] Tracey: And it didn't matter how hard I tried to assert my boundaries earlier on in this business journey. It. felt very challenging and very difficult and very toxic for me to assert my boundaries all the time when I was receiving phone calls constantly about, have I done this? How long did it take? Well, how much do I have left on the retainer this month?
[00:05:40] Tracey: And that is not in the spirit of a retainer arrangement that I was trying to create for her. So it was horrible. I can actually hand on heart now say it was horrible, but the lesson here and why I'm sharing this is because there's so much value to take from what went wrong and I'm a firm believer that things don't happen to us.
[00:06:03] Tracey: They happen for us. So that we can learn. And sure, I've made that same mistake a few times. I've got to say, I'm that person that, that says, learn from others. You don't all have to jump off a cliff to know it's going to hurt. And I stand by that. But also, unfortunately, sometimes I need to make the same mistake a few times for it to really sink in.
[00:06:22] Tracey: And earlier on in my business journey, that really came from a position of self doubt. So I doubted myself. Someone would ask me to do something and they try to convince me that it would work and it was the right thing. And then I would doubt myself. We've all got stories like that, but that's what makes this person the worst client I've ever had.
[00:06:42] Tracey: She's not a bad person. there were many people of whom I knew, who knew her that said she was a good business person. my version or definition of, of a great business person or a good business person clearly differs to theirs, but that's okay.
[00:06:55] Tracey: We don't all need to be the same. But what I learned from this was very clearly if someone doesn't respect. themselves. If someone doesn't respect their team, There's a very high chance they're not going to respect you or the quality of services that you deliver. I take that with me now, always.
[00:07:17] Tracey: Respect. Is it there? Look at how they treat others. Look at how they treat their team. What are they reaching out to me for? What's their attitude to their client journey and their clients? Is it all about the money? I don't care about the client journey and to hell with them. They can't have this. Is it like that?
[00:07:32] Tracey: Because if it is, we're not aligned. And so I know very early on how to beautifully and eloquently say no or part ways. If though the respect is there. And I look at how they treat their clients and how they think about their clients and how important their clients are to them and how they treat their team and how important their team is.
[00:07:51] Tracey: If all of that's there, then I'm in with a very good chance of being in a position where I love working with this client. And these things are important, but I learned that from this worst client experience that I'm sharing with you. The other thing, the other massive thing that I learned from that client experience was.
[00:08:13] Tracey: The value of backing myself, the value of not doubting myself. And I don't say that in a cliche way. I say that in a really earnest, authentic way that when we doubt ourselves, the decisions that follow are rarely going to serve us. the decisions that follow when we doubt ourselves are rarely going to serve us.
[00:08:36] Tracey: And there have been times since that particular client where I have against my own better judgment agreed to take a client on or agreed to a client request. When deep down intuitively, I knew it was wrong. I knew I didn't want to do it. It's not going to pan out. And every time I've gone against that, I have lived to regret it.
[00:08:59] Tracey: Nothing dire, nothing earth shattering. But when you run a business the way I do and you magnetize beautifully aligned clients, and you're really clear about who it is you like to work with and the value. That you bring for me, one of my ethos, one of my key ethos is enriching lives. So that's what I've out to do when I'm doubting at the beginning, whether this is going to be a positive relationship, whether we really are aligned in the way that We want to work when I'm doubting that so early on, nothing good has come from me pushing that aside and doing it anyway.
[00:09:37] Tracey: It's probably a half a dozen times if I'm going to be really honest with you. And I'm always very honest and open on this podcast. So there's been about a half a dozen times since that worst client experience where I've lived to regret it. Like I said, not earth shattering, no massive consequence, just a really unpleasant experience.
[00:09:54] Tracey: And these things don't end well. So they do come to an end. The point will come where boundaries need to be asserted. One needs to protect one's own business and client workflow. So boundaries are asserted and that's not ever taken well by the other party when we're in the situation where it's not panning out because it's not working the way you want to, when you assert your boundaries, chances are it's not going to be taken well.
[00:10:20] Tracey: So those are my two. Biggest takeaways from that worst client experience, doing something that I didn't want to do for someone who lacks the level of respect that's important to me. It's not going to end well. So that's what made it the worst client experience. I don't have any other worst client experiences to share in comparison to that.
[00:10:42] Tracey: That's a standout. There's not even a close second. And I feel so grateful to be able to say that. That I don't have those poor negative client experiences anymore. Because like I've said, and I say so often. Things happen for us, not to us. That's my belief and I stand by that.
[00:11:00] Tracey: And I took that. It was hard at the time. My gosh, it was really hard. And I really did feel like I was beating myself up for quite a while trying to bring that to an end. And it didn't end well, when I did assert those boundaries and that was unpleasant. So I needed to sit with that for a while and, and just let that be so I could learn from it.
[00:11:15] Tracey: And now I'm sharing it with you. With you, so that's the story that I share when people ask, what was your worst client and I almost feel like it's a bit disappointing for people to hear because it's not salacious and it's not back from those litigation days and people doing all sorts of horrendous things to each other when they're embroiled in dispute.
[00:11:32] Tracey: It just wasn't anything like that. I hope that some of this has resonated for you and I'd encourage you now to go away and have a think about what have been your unpleasant or even worst client experiences and what have we learned from that? are there any little nuggets that you can take away from that to implement or tweak?
[00:11:50] Tracey: Processes and systems, whether it's discovery calls or clarity calls or onboarding or whatever it might be to detect those early red flags so that we don't end up in positions where we've got those unpleasant client relationships. And so we can all sit here and share our business journey with others with pure gratitude for the beautiful clients that we get to work with because the negative client experiences are few and far between.
[00:12:15] Tracey: I hope you've enjoyed it. I've shared this with you as always. Thank you for listening. I'll catch you next week.
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